EP0975586B1 - Composes d'oxime, leur utilisation et intermediaires pour leur production - Google Patents

Composes d'oxime, leur utilisation et intermediaires pour leur production Download PDF

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Publication number
EP0975586B1
EP0975586B1 EP98911012A EP98911012A EP0975586B1 EP 0975586 B1 EP0975586 B1 EP 0975586B1 EP 98911012 A EP98911012 A EP 98911012A EP 98911012 A EP98911012 A EP 98911012A EP 0975586 B1 EP0975586 B1 EP 0975586B1
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Prior art keywords
dichloro
propenyloxy
phenoxy
alkyl
oxime
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EP98911012A
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German (de)
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EP0975586A2 (fr
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Hiroshi Ikegami
Keiichi Izumi
Masaya Suzuki
Noriyasu Sakamoto
Shigeru Saito
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/36—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C251/38—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atoms of the oxyimino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Definitions

  • the present invention relates to oxime compounds, their use, and intermediates for their production.
  • the present invention further provides compounds of formula (13) wherein R 2 , R 3 , R 7 , R 19 , R 20 , and j are as defined above, and R 41 is 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, or 3-bromo-3-chloro-2-propenyl, which are useful as the intermediates for the production of the present compounds.
  • the present invention further provides compounds of formula (14) wherein R 2 , R 3 , R 7 , R 19 , R 20 , R 29 , R 30 , R 41 , j, and v are as defined above, which are useful as the intermediates for the production of the present compounds.
  • the present invention further provides phenol compounds of formula (50) wherein R 1 , R 2 , R 3 , a, X, and Z are as defined above, with the proviso that when X is X 1 , R 6 is not hydrogen, which are useful as the intermediates for the production of the present compounds.
  • the C 1 -C 11 alkyl represented by R 8 or R 9 may include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpropyl, n-hexyl, isohexyl, 2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl, 1,3-dimethylbutyl, n-heptyl, 1-ethyl-1-methylbutyl, n-octyl, 1-methylheptyl, n-nonyl, n-decyl, and n-undecyl.
  • the C 1 -C 3 haloalkyl represented by R 1 , R 2 , R 3 , R 7 , R 10 , R 15 , R 17 , R 18 , or R 40 may include, for example, trifluoromethyl, difluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, perfluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,
  • the C 2 -C 6 haloalkyl represented by R 6 , R 16 , or R 42 may include, for example, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1, 3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2-iodopropyl,
  • the C 1 -C 6 haloalkyl represented by R 8 or R 9 may include, for example, trifluoromethyl, trichloromethyl, difluoromethyl, bromodifluoromethyl, 2,2, 2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloro
  • the C 1 -C 3 alkoxy represented by R 1 , R 2 , R 3 , or R 40 may include methoxy, ethoxy, n-propyloxy, and isopropyloxy.
  • the C 1 -C 6 alkoxy represented by R 10 , R 17 , and R 18 may include, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, 1-ethylpropylaxy, n-hexyloxy, isohexyloxy, 2-ethylbutyloxy, 1-methylpentyloxy, 1-ethylbutyloxy, 3-methylpentyloxy, and 1,3-diemthylbutyloxy.
  • the C 1 -C 3 haloalkoxy represented by R 1 , R 2 , R 3 , R 10 , R 17 , R 18 , or R 40 may include, for example, trifluoromethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 1-chloroethoxy, 1-bromoethoxy, perfluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxyethoxy, 2,2,2-tribromoethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2-dichloroethoxy, 2,2-d
  • the C 3 -C 6 alkenyl represented by R 6 , R 16 , or R 42 may include, for example, allyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3
  • the C 3 -C 6 haloalkenyl represented by R 6 , R 16 , or R 42 may include, for example, 3-chloro-2-propenyl, 3-bromo-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 2-chloromethyl-2-propenyl, 4-chloro-2-butenyl, 3-chloro-4,4,4-trifiuoro-2-butenyl, 3-bromo-4,4,4-trifluoro-2-butenyl, 3,4-dichloro-4,4-difluoro-2-butenyl, 3,4,4, 4-tetrafluoro-3-butenyl
  • the C 3 -C 6 alkynyl represented by R 6 , R 16 , or R 42 may include, for example, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, and 2-ethyl-3-butynyl.
  • the C 3 -C 6 haloalkynyl represented by R 6 , R 16 , or R 42 may include, for example, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 4-chloro-2-butynyl, 4-chloro-3-butynyl, 4-bromo-2-butynyl, 4-bromo-3-butynyl, 5-chloro-4-pentynyl, 4-chloro-1-methyl-2-butynyl, 4-chloro-1-methyl-3-butynyl, 4-chloro-2-methyl-3-butynyl, 5-bromo-4-pentynyl, 4-bromo-1-methyl-2-butynyl, 4-bromo-1-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 6-chloro-5-hexynyl, and 6-bromo-5-hexynyl.
  • the C 2 -C 6 alkenyl R 8 , R 9 , R 10 , R 15 , R 17 , or R 18 may include, for example, vinyl, 1-propenyl, isopropenyl, 1-butenyl, allyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl
  • the C 2 -C 6 haloalkenyl represented by R 8 , R 9 , R 10 , R 17 , or R 18 may include, for example, 2-chloroethenyl, 2-bromoethenyl, 2,2-dichloroethenyl, 2,2-dibromoethenyl, 3-chloro-2-propenyl, 3-bromo-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 2-chloromethyl-2-propenyl, 4-chloro-2-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, 3-bromo-4,4,4
  • the C 2 -C 6 alkynyl represented by R 8 ,R 9 , R 10 , R 17 , or R 18 may include, for example, ethynyl, 1-propynyl, 1-butynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, and 2-methyl-3-butynyl.
  • the C 2 -C 6 haloalkynyl represented by R 8 ,R 9 , R 10 , R 17 , or R 18 may include, for example, 2-chloroethynyl, 2-bromoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 4-chloro-2-butynyl, 4-chloro-3-butynyl, 4-bromo-2-butynyl, 4-bromo-3-butynyl, 5-chloro-4-pentynyl, 4-chloro-1-methyl-2-butynyl, 4-chloro-1-methyl-3-butynyl, 4-chloro-2-methyl-3-butynyl, 5-bromo-4-pentynyl, 4-bromo-1-methyl-2-butynyl, 4-bromo-1-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 5-bro
  • the C 3 -C 6 cycloalkyl represented by R 7 , R 15 , R 16 , R 17 , or R 42 may include cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
  • the C 2 -C 10 alkoxyalkyl represented by R 8 or R 9 may include, for example, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, 2-methoxyethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl, 2-methoxy-1-methylethyl, 2-propyloxyethyl, 2-isopropyloxyethyl, 2-ethoxypropyl, 2-ethoxy-1-methylethyl, 2-methoxybutyl, 1-ethyl-2-methoxyethyl, 3-ethoxypropyl, 3-methoxybutyl, 3-methoxy-2-methylpropyl, 3-methoxy-1-methylpropyl 2-butoxyethyl, 3-methoxy-3-methylbutyl, and 2-butoxy-1-methyl
  • the C 2 -C 10 alkylthioalkyl represented by R 8 or R 9 may include, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 2-methylthiomethyl, 1-methylthioethyl, 2-ethylthioethyl, 1-ethylthioethyl, 3-methylthiopropyl, 2-methylthiopropyl, 1-methylthiopropyl, 2-methylthio-1-methylethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-ethylthiopropyl, 2-ethylthio-1-methylethyl, 2-methylthiobutyl, 1-ethyl-2-methylthioethyl, 3-ethylthiopropyl, 3-methylthiobutyl, 2-methyl-3-methylthiopropyl, 1-methyl-3-methylthiopropyl, 4-methylthiobuty
  • the C 3 -C 6 alkenyloxy represented by R 10 , R 17 , or R 18 may include, for example, allyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy, 1-ethyl-2-propenyloxy, 2-ethyl-2-propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pen
  • the C 3 -C 6 haloalkenyloxy represented by R 10 , R 17 , or R 18 may include, for example, 3-chloro-2-propenyloxy, 3-bromo-2-propenyloxy, 2-chloro-2-propenyloxy, 2-bromo-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 3,3-dibromo-2-propenyloxy, 3,3-difluoro-2-propenyloxy, 2,3-dichloro-2-propenyloxy, 2,3-dibromo-2-propenyloxy, 2-chloromethyl-2-propenyloxy, 4-chloro-2-butenyloxy, 3-chloro-4,4,4-trifluoro-2-butenyloxy, 3-bromo-4,4,4-trifluoro-2-butenyloxy, 3,4-dichloro-4,4-difluoro-2-butenyloxy, 3,4,4,
  • the C 3 -C 6 alkynyloxy represented by R 10 , R 17 , or R 18 may include, for example, 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-ethyl-2-butynyloxy, 1-ethyl-3-butynyloxy, and 2-ethyl-3-butynyloxy.
  • the C 3 -C 6 haloalkynyloxy represented by R 10 , R 17 , or R 18 may include, for example, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 4-chloro-2-butynyloxy, 4-chloro-3-butynyloxy, 4-bromo-2-butynyloxy, 4-bromo-3-butynyloxy, 5-chloro-4-pentynyloxy, 4-chloro-1-methyl-2-butynyloxy, 4-chloro-1-methyl-3-butynyloxy, 4-chloro-2-methyl-3-butynyloxy, 5-bromo-4-pentynyloxy, 4-bromo-1-methyl-2-butynyloxy, 4-bromo-1-methyl-3-butynyloxy, 4-bromo-2-methyl-3-butynyloxy, 6-chloro-5-hexynyloxy, and 6-bro
  • the C 1 -C 3 haloalkylthio represented by R 17 or R 18 may include, for example, trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 2-chloro-1,1,2-trifluoroethylthio, 2-bromo-1,1,2-trifluaroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio, 1,1,2,2,2-pentafluoroethylthio, 3-fluoropropylthio, 3-chloropropylthio, 3-bromopropylthio, 2,2,3,3,3-pentafluoropropylthio, and 3,3,3-trifluoropropylthio.
  • the C 1 -C 2 alkylsulfinyl represented by R 17 or R 18 may include methylsulfinyl or ethylsulfinyl.
  • the C 1 -C 2 haloalkylsulfinyl represented by R 17 or R 18 may include, for example, trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, and perfluoroethylsulfinyl.
  • the C 1 -C 2 haloalkylsulfonyl represented by R 17 or R 18 may include, for example, trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, and perfluoroethylsulfonyl.
  • the C 2 -C 4 alkoxyalkyl represented by R 17 or R 18 may include, for example, methoxymethyl, ethoxymethyl, propyloxymethyl, isopropyloxymethyl, 2-methoxyethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl, and 2-methoxy-1-methylethyl.
  • the (C 1 -C 2 alkyl)aminocarbonyl represented by R 17 may include methylaminocarbonyl or ethylaminocarbonyl.
  • the di(C 1 -C 2 alkyl)aminocarbonyl represented by R 17 may include dimethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl, or diethylaminocarbonyl.
  • the (C 1 -C 6 alkoxy)carbonyl represented by R 17 may include, for example, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, tert-pentyloxycarbonyl, 1-ethylpropyloxycarbonyl, n-hexyloxycarbonyl, isohexyloxycarbonyl, 2-ethylbutyloxycarbonyl, 1-methylpentyloxycarbonyl, 1-ethylbutyloxycarbonyl, 3-methylpentyloxycarbonyl, and 1,3-dimethylbutylcarbonyl.
  • the C 5 -C 6 cycloalkenyl represented by R 17 may include 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, or 3-cyclohexenyl.
  • the C 3 -C 6 cycloalkyloxy represented by R 17 may include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, or cyclohexyloxy.
  • the C 5 -C 6 cycloalkenyloxy represented by R 17 may include 1-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy, 1-cyclohexenyloxy, 2-cyclohexenyloxy, or 3-cyclohexenyloxy.
  • the 3,3-dihalogeno-substituted-2-propenyl represented by R 4 may include, for example, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3-bromo-3-chloro-2-propenyl, 3-chloro-3-fluoro-2-propenyl, and 3-bromo-3-fluoro-2-propenyl.
  • the C 3 -C 7 cycloalkyl optionally substituted with C 1 -C 4 alkyl, which is represented by R 6 , R 8 , or R 9 may include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylcyclopentyl, 3-methylcyclopentyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-n-propylcyclohexyl, 4-isopropylcyclohexyl, and 4-tert-butylcyclohexyl.
  • the C 4 -C 10 cycloalkylalkyl optionally substituted with C 1 -C 4 alkyl on the ring thereof, which is represented by R 6 , R 8 , or R 9 , may include, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl, (2-methylcyclopropyl)methyl, 2-(2-methylcyclopropyl)ethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, 2-cyclohexylethyl, and 3-cyclohexylpropyl.
  • the C 5 -C 6 cycloalkenyl optionally substituted with C 1 -C 4 alkyl, which is represented by R 6 , R 8 , or R 9 , may include, for example, 2-cyclopentenyl, 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 3,5,5-trimethyl-2-cyclohexenyl, and 3-methyl-2-cyclohexenyl.
  • the C 6 -C 8 cycloalkenylalkyl optionally substituted with C 1 -C 4 alkyl on the ring thereof, which is represented by R 6 , R 8 , or R 9 , may include, for example, (1-cyclopentenyl)methyl, (2-cyclopentenyl)methyl, (1-cyclohexenyl)-methyl, (2-cyclohexenyl)methyl, (3-cyclophexenyl)methyl, and 2-(3-cyclohexenyl)ethyl.
  • the halogen in the phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy, which is represented by R 7 , R 15 , R 16 , R 17 , R 18 , or R 42 , may include fluorine, chlorine, bromine, or iodine.
  • the C 1 -C 4 alkyl in the phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy, which is represented by R 7 , R 15 , R 16 , R 17 , R 18 , or R 42 , may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl.
  • the C 1 -C 3 haloalkyl in the phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy, which is represented by R 7 , R 15 , R 16 , R 17 , R 18 , or R 42 , may include, for example, trifluoromethyl, difluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, perfluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloro
  • the C 1 -C 3 alkoxy in the phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy, which is represented by R 7 , R 15 , R 16 , R 17 , R 18 , or R 42 , may include methoxy, ethoxy, n-propyloxy, or isopropyloxy.
  • the C 1 -C 3 haloalkoxy in the phenyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy, which is represented by R 7 , R 15 , R 16 , R 17 , R 18 , or R 42 , may include, for example, trifluoromethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 1-chloroethoxy, 1-bromoethoxy, perfluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-tribromoeth
  • the C 1 -C 4 alkyl in the benzyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy on the ring thereof, which is represented by R 7 , R 16 , R 17 , or R 42 , may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl.
  • the C 1 -C 3 alkoxy in the benzyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy on the ring thereof, which is represented by R 7 , R 16 , R 17 , or R 42 , may include methoxy, ethoxy, n-propyloxy, or isopropyloxy.
  • the C 1 -C 3 haloalkoxy in the benzyl optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy on the ring thereof, which is represented by R 7 , R 16 , R 17 , or R 42 , may include, for example, trifluoromethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 1-chloroethoxy, 1-bromoethoxy, perfluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-triluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-tribromoethoxy,
  • the halogen in the phenoxy or benzyloxy optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy on the ring thereof, which is represented by R 17 may include fluorine, chlorine, bromine, or iodine.
  • the C 1 -C 4 alkyl in the phenoxy or benzyloxy optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy on the ring thereof, which is represented by R 17 , may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl.
  • the C 1 -C 3 haloalkyl in the phenoxy or benzyloxy optionally substituted with halogen, C 1 -C 4 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, or C 1 -C 3 haloalkoxy on the ring thereof, which is represented by R 17 , may include, for example, trifluoromethyl, difluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, perfluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,2,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribrom
  • the halogen in the methylenedioxy optionally substituted with halogen or C 1 -C 3 alkyl, which is represented by R 17 and which is formed from two adjacent R 17 's combined together at their ends when b is 2 to 5, may include fluorine, chlorine, bromine, or iodine.
  • the halogen in the ethylenedioxy optionally substituted with halogen or C 1 -C 4 alkyl, which is represented by R 17 and which is formed from two adjacent R 17 's combined together at their ends when b is 2 to 5, may include fluorine, chlorine, bromine, or iodine.
  • the C 1 -C 3 alkyl in the ethylenedioxy optionally substituted with halogen or C 1 -C 3 alkyl, which is represented by R 17 and which is formed from two adjacent R 17 's combined together at their ends when b is 2 to 5, may include methyl, ethyl, n-propyl, and isopropyl.
  • the solvent which can be used may include, for example, hydrocarbons such as benzene, xylene, and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene.
  • hydrocarbons such as benzene, xylene, and toluene
  • ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane
  • halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene.
  • the molar ratio of the starting materials and base to be used in the reaction may be suitably selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
  • the reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
  • the reaction is preferably effected in the presence of an appropriate dehydrating agent and, if necessary, in an inert solvent.
  • Production process F (for the present compounds wherein X is X 1 , with the proviso that R 6 is not hydrogen, T 1 -4, T 1 -5, T 1 -6, or T 1 -7)
  • Production process G (for the present compounds wherein Y and Z are both oxygen, X is X 1 , A 1 is A 1 -8, and e1 is 0, with the proviso that R 6 is not hydrogen)
  • the solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C 1 -C 4 ) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
  • ketones such as acetone, methyl eth
  • the reaction temperature can be usually selected in the range of - 20°C to the boiling point of a solvent used in the reaction or 150°C.
  • the molar ratio of the starting materials and base to be used in the reaction may be suitably selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
  • Production process H (for the present compounds wherein Y and Z are both oxygen, X is X 2 , A 2 is A 2 -4, and e1 is 0)
  • the reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
  • the solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C 1 -C 4 ) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
  • ketones such as acetone, methyl eth
  • the base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C 1 -C 4 ) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine.
  • catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (27).
  • the reaction temperature can be usually selected in the range of -20°C to the boiling point of a solvent used in the reaction or 150°C.
  • the molar ratio of the starting materials and base to be used in the reaction may be freely selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
  • the reaction can be effected in an inert solvent and, if necessary, in the presence of a base.
  • the solvent which can be used may include, for example, alcohols such as methanol and ethanol; ethers such as diethyl ether, tetrahydrofuran, and dioxane; pyridine; and water.
  • the carbonyl compound of formula (30) may also be used as the solvent. If necessary, these solvents may also be used in admixture.
  • the base which can be used may include, for example, triethylamine, pyridine, and sodium acetate.
  • the O-substituted hydroxylamine compound as the starting material is usually used in the form of an inorganic acid salt such as hydrochloride.
  • the molar ratio of the starting materials and reagents to be used in the reaction may be suitably selected; however, it is preferred that the reaction of the carbonyl compound of formula (30) and the O-substituted hydroxylamine compound of formula (29) or a salt thereof is effected at the equimolar ratio or a ratio close thereto.
  • the amount of base to be used, if necessary, in the reaction is preferably 1 mole or more relative to 1 mole of the compound of formula (29).
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
  • the solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C 1 -C 4 ) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
  • ketones such as acetone, methyl eth
  • the base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C 1 -C 4 ) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine.
  • catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (31).
  • the molar ratio of the starting materials and base to be used in the reaction may be freely selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
  • Production process K (for the compounds wherein X is X 1 and R 6 is T 1 -4, T 1 -5, or T 1 -7)
  • the reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
  • the solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C 1 -C 4 ) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
  • ketones such as acetone, methyl eth
  • the base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C 1 -C 4 ) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In particular, organic bases such as triethylamine or pyridine are preferably used.
  • the molar ratio of the starting materials and base to be used in the reaction may be freely selected; however, it is favorable that the reaction is effected with the compound of formula (33), (34), (35), or (36) and the base in an amount of 1 to 5 moles, respectively, relative to 1 mole of the compound of formula (24).
  • Production process L (for the present compounds wherein X is X 1 and R 6 is T 1 -6)
  • reaction is effected, if necessary, in the presence of an appropriate catalyst and in an inert solvent.
  • the solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C 1 -C 4 ) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; and hydrocarbons such as toluene, benzene, and xylene. If necessary, these solvents may also be used in admixture.
  • ketones such as acetone, methyl ethyl
  • bases such as triethylamine, pyridine, and sodium acetate
  • acids such as aluminum chloride, hydrogen chloride, and boron trifluoride ether complex (BF 3 ⁇ (C 2 H 5 ) 2 O), can be used.
  • the reaction temperature although it can be usually selected in the range of -20°C to the boiling point of a solvent used in the reaction, is more preferably in the range of -5°C to the boiling point of the solvent used in the reaction.
  • the molar ratio of the starting materials be used in the reaction may be freely selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
  • reaction is effected in the presence of an appropriate acid catalyst and in an inert solvent.
  • the solvent which can be used may include, for example, hydrocarbons such as toluene, benzene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, and dioxane, dialkyl (e.g., C 1 -C 4 ) ethers (e.g., diethyl ether, diisopropyl ether); and esters such as ethyl acetate. If necessary, these solvents may also be used in admixture.
  • hydrocarbons such as toluene, benzene, and xylene
  • halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene
  • ethers such as 1,2-dimethoxyethane, tetra
  • the acid catalyst which can be used may include, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, perchloric acid, sulfuric acid, nitric acid, and phosphoric acid; and organic acids such as trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, and camphorsulfonic acid.
  • inorganic acids such as hydrochloric acid, hydrobromic acid, perchloric acid, sulfuric acid, nitric acid, and phosphoric acid
  • organic acids such as trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, and camphorsulfonic acid.
  • sulfuric acid is preferably used.
  • the reaction temperature although it can be usually selected in the range of -50°C to 50°C or the boiling point of a solvent used in the reaction, is usually in the range of 0°C to 30°C.
  • the molar ratio of the starting materials to be used in the reaction may be suitably selected; however, the reaction is preferably effected with the use of isobutene in an amount of 1 mole or more relative to 1 mole of the compound of formula (24).
  • reaction mixture After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
  • optical isomers based on the presence of at least one asymmetric carbon atom, and the optical isomers having biological activity, whether they are either in (+)-form or in (-)-form, and their mixtures at any ratio are, of course, included within the scope of the present invention.
  • geometrical isomers based on the presence of at least one double bond, and the geometrical isomers having biological activity, whether they are either in cis-form or in trans-form, and their mixtures at any ratio are, of course, included within the scope of the present invention.
  • the compounds of formula (12), which are useful as the intermediates for the production of the present compounds, also have insecticidal/acaricidal activity and can therefore be formulated or used as the active ingredients of insecticidal/acaricidal agents, in the same manner as the case of the present compounds.
  • (R 1 ) a , R 2 , R 3 , and M 2 are as defined in Table 1 below, and R 6 is as defined in Tables 2 to 19 below.
  • R 8 and R 9 are as defined in Tables 11. to 17.
  • R 8 R 9 CH 3 - H CH 3 CH 2 - H CH 3 CH 2 CH 2 - H (CH 3 ) 2 CH- H CH 3 CH 2 CH 2 CH 2 - H (CH 3 ) 2 CHCH 2 - H CH 3 CH 2 CH(CH 3 )- H (CH 3 ) 3 C- H CH 3 CH 2 CH 2 CH 2 - H (CH 3 ) 2 CHCH 2 CH 2 - H CH 3 CH 2 CH(CH 3 )CH 2 - H (CH 3 ) 3 CCH 2 - H CH 3 CH 2 CH 2 CH(CH 3 )- H (CH 3 ) 2 CHCH(CH 3 )- H (CH 3 CH 2 ) 2 CH- H CH 3 CH 2 CH 2 CH 2 CH(CH 3 )- H (CH 3 CH 2 ) 2 CH- H CH 3 CH 2 CH 2 CH(CH 3 )- H (CH 3 CH 2 ) 2 C(CH 3 CH 2 )- H (CH 3 CH 2 ) 2 CH
  • the compounds of formula (15) as the intermediates for the production of the present compounds can be produced, for example, according to the following schemes I to VI. wherein all the variables are as defined above, with the proviso that R 6 is not hydrogen. wherein all the variable are as defined above, with the proviso that R 6 is not hydrogen. wherein all the variable are as defined above, with the proviso that R 6 is not hydrogen. wherein all the variable are as defined above, with the proviso that R 6 is not hydrogen. wherein TBDMSCI is tert-butyldimethylsillyl chloride, Z 1 is oxygen or sulfur, and the other variables are as defined above, with the proviso that R 6 is not hydrogen. wherein all the variables are as defined above, with the proviso that R 6 is not hydrogen.
  • halide compounds of formula (16) and alcohol compounds of formula (17), both as the intermediates for the production of the present compounds, are commercially available or can be produced, for example, according to the publications: J. Org. Chem., 56, 1037-1041 (1991); Izvest. Akad. Nauk S.S.S.R., Otdel. Khim. Nauk, 1960 , 447-451 [CA (Chemical Abstracts) vol. 54, 22344d]; and Doklady Akad. Nauk S.S.S.R. 132 , 606-608 (1960) [CA (Chemical Abstracts) vol. 54, 22331h], or according to the following scheme VIII. wherein L 1 is chlorine or bromine, L 2 is mesyloxy or tosyloxy, and M is halogen.
  • the compounds of formula (22) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XI, XII, XIII, XIV, or XV.
  • Y 1 is oxygen or NH
  • R 52 is a protecting group for the hydroxyl group of phenol or for the amino group of aniline, such as benzoyl, acetyl, or tert-butylmethylsillyl (TBDMS), and the other variables are as defined above.
  • R 53 is methyl or ethyl
  • R 54 is a protecting group for the hydroxyl group of phenol, such as benzoyl or acetyl, and the other variables are as defined above. wherein all the variables are as defined above.
  • R 53 is methyl or ethyl
  • R 55 is a protecting group for the hydroxyl group of phenol, such as benzyl
  • DIBAL means diisobutylaluminum hydride
  • R 55 is a protecting group for the hydroxyl group of phenol, such as benzyl
  • R 56 is acetyl or benzoyl
  • PCC means pyridinium chlorocromate, and the other variables are as defined above.
  • the compounds of formula (33), (34), (35), (36), or (37), as the intermediates for the production of the present compounds, are commercially available or can be produced by the methods widely known in the art or by the methods as described in the publications: [compounds of formula (33) wherein J is sulfur] J. Org. Chem., 30 , 1284 (1965); [compounds of formula (35) wherein J is oxygen] J. Am. Chem. Soc., 81 , 714 (1959); [compounds of formula (35) wherein J is sulfur] Justus Liebigs Ann. Chem., 590 , 123 (1954).
  • the compounds of formula (19) or (20) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XVII. wherein all the variables are as defined above.
  • the compounds of formula (39) can be produced, for example, according to the following schemes XVIII-1 to XVIII-9.
  • R 101 is L or Q 4 H
  • Q 4 is oxygen, sulfur, or NR 34
  • R 34 is hydrogen or C 1 -C 3 alkyl
  • R 102 is a protecting group for alcohols, such as benzoyl
  • a 11 is A 11 -7, A 11 -8, A 11 -9, A 11 -10, A 11 -11, or A 11 -12 of formula (40)
  • the compounds of formula (25) as the intermediates for the production of the present compounds can be produced, for example, according to scheme XIV. where all the variables are as defined above.
  • R 106 is methyl or ethyl
  • R 107 is C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, or phenyl or benzyl, each of which may be optionally substituted with C 1 -C 4 alkyl or C 1 -C 3 alkoxy
  • the other variables are as defined above. wherein all the variables are as defined above. wherein all the variables are as defined above. wherein all the variables are as defined above. wherein all the variables are as defined above.
  • the compounds of formula (19) or (20) wherein X is X 2 can be produced, for example, according to the following scheme XXV.
  • L 3 is halogen (e.g., chlorine, bromine, iodine), mesyloxy, or tosyloxy
  • R 151 is a protecting group for alcohols, such as described in PROTECTIVE GROUPS IN ORGANIC SYNTHESIS, T.W. Greene, P.G.M. Wuts, A WILEY-INTERSCIENCE PUBLICATION, JOHN WILEY & SONS, INC., pp. 10-142; e.g., benzoyl, and the other variables are as defined above.
  • the compounds of formula (48) or (49) in the scheme XXV can be produced, for example, according to the following schemes XXVI to XXXXIII. wherein all the variables are as defined above.
  • L 4 is halogen (e.g., chlorine, bromine, iodine), mesyloxy, or tosyloxy
  • Q 8 is oxygen, sulfur, or NR 33
  • R 33 is hydrogen or C 1 -C 3 alkyl
  • the other variables are as defined above.
  • Q 9 is oxygen, sulfur, or NR 34
  • R 34 is hydrogen or C 1 -C 3 alkyl, and the other variables are as defined above.
  • the compounds of formula (29) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XXXXVIII. wherein all the variables are as defined above.
  • the compounds of formula (32) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XXXXIX. wherein all the variables are as defined above.
  • the solid carrier which can be used in the formulation may include, for example, fine powder or granules of clay materials such as kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, Fubasami clay, and acid clay; various kinds of talc, ceramics, and other inorganic minerals such as sericite, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica; and chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride.
  • clay materials such as kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, Fubasami clay, and acid clay
  • various kinds of talc, ceramics, and other inorganic minerals such as sericite, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica
  • chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea
  • the liquid carrier may include, for example, water; alcohols such as methanol and ethanol; ketones such as acetone and methyl ethyl ketone; hydrocarbons such as hexane, cyclohexane, kerosene, and light oil; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and isobutyronitrile; ethers such as diisopropyl ether and dioxane; acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide; halogenated hydrocarbons such as dichloromethane, trichloroethane, and carbon tetrachloride; dimethyl sulfoxide; and vegetable oils such as soybean oil and cottonseed oil.
  • alcohols such as methanol and ethanol
  • ketones such as acetone and methyl ethyl ketone
  • hydrocarbons such as
  • the surfactant may include, for example, alkyl sulfates, alkyl sulfonates, alkyl arylsulfonates, alkyl aryl ethers and their polyoxyethylene derivatives, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
  • the auxiliaries such as fixing agents or dispersing agents may include, for example, casein, gelatin, polysaccharides such as starch, gum arabic, cellulose derivatives, and alginic acid, lignin derivatives, bentonite, sugars, and synthetic water-soluble polymers such as polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acid.
  • the stabilizer may include, for example, PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (mixtures of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids, and their esters.
  • PAP isopropyl acid phosphate
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • BHA mixturetures of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol
  • vegetable oils mineral oils
  • surfactants fatty acids, and their esters.
  • the formulations thus obtained are used as such or after diluted with water. Furthermore, they may be used in admixture with or separately but simultaneously with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners and/or animal.
  • the insecticide, nematocide and/or acaricide which can be used may include, for example, organophosphorus compounds such as Fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate], Fenthion [O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl)phophorothioate], Diazinon [O,O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-ylphosphorothioate], Chlorpyriphos [O,O-diethyl-O-3,5,6-trichloro-2-pyridylphoaphorothioate], Acephate [O,S-dimethylacetylphosphoramidothioate], Methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethylphosphorodi
  • the present compounds When used as the active ingredients of insecticidal/acaricidal agents for epidemic prevention, they are usually applied after diluted with water to a typical concentration of 0.1 to 500 ppm in the case of emulsifiable concentrates, wettable powders, flowable, or similar formulations; or they are applied as such in the case of oil sprays, aerosols, fumigants, poisonous baits, or similar formulations.
  • the application amount and concentration may vary depending upon the conditions including types of formulations, times, places and methods of application, kinds of noxious insects, mites and ticks, and degree of damage, and they can be increased or decreased without limitation to the above range.
  • Production Example 2 Production of the present compound (12) by production process F
  • Production Example 7 Production of the present compound (74) by production process C
  • Production Example 8 Production of the present compound (147) by production process E
  • Production Example 10 Production of the present compound (234) by production process E
  • Production Example 11 Production of the present compound (104) by production process E
  • Production Example 12 Production of the present compound (177) by production process K
  • Production Example 14 Production of the present compound (180) by production process K
  • Production Example 17 Production of the present compound (218) by production process L
  • Production Example 18 Production of the present compound (213) by production process F
  • Production Example 22 Production of the present compound (210) by production process D
  • Production Example 25 Production of the present compound (104) by production process M
  • diethyl ether solution have the weight of 30 g.
  • hydrochloric acid were poured into a reaction vessel containing 0.37 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal. After stirring at room temperature for 2 hours, the reaction mixture was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product.
  • the intermediate compounds produced in Reference Production Example 10 or 12 can also be used as the starting material in Reference Production Example 7, and the intermediate compounds produced in Reference Production Example 11 or 13 can also be used as the starting material in Reference Production Example 8.
  • Intermediate compounds 182) to 188) can also be sued as the starting materials for the production of intermediate compounds 170) to 181) of formula (19).
  • each of the present compounds (1) to (687) is added to a mixture of 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic hydrated silicon oxide fine powder, and 54 parts of diatomaceous earth.
  • the mixture is stirred with a mixer to give a 20% wettable powder of each compound.
  • each of the present compounds (1) to (687) To five parts of each of the present compounds (1) to (687) are added 5 parts of synthetic hydrated silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite, and 55 parts of clay, and the mixture is well stirred. A suitable amount of water is added to the mixture, which is further stirred, granulated with a granulator, and air-dried to give a 5% granule of each compound.
  • each of the present compounds (1) to (687) is mixed with 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol.
  • the mixture is pulverized into fine particles having a particle size of not more than 3 ⁇ m with a sand grinder, to which 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added and then 10 parts of propylene glycol is added.
  • the mixture is stirred to give a 20% flowable of each compound.
  • 0.1 part of each of the present compounds (1) to (687), 0.2 part of tetramethrin, 0.1 part of d-phenothrin, and 10 parts of trichloroethane are dissolved in 59.6 parts of deodorized kerosine, and the solution is put in an aerosol vessel.
  • the vessel is equipped with a valve, through which 30 parts of a propellant (liquefied petroleum gas) is charged under increased pressure to give an oil-based aerosol of each compound.
  • a propellant liquefied petroleum gas
  • An aerosol vessel is filled with a mixture of 0.2 part of each of the present compounds (1) to (687), 0.2 part of d-allethrin, 0.2 part of d-phenothrin, 5 parts of xylene, 3.4 parts of deodorized kerosine, and 1 part of an emulsifier (ATMOS 300 available from Atlas Chemical Co.); and 50 parts of pure water.
  • the vessel is equipped with a valve, through which 40 parts of a propellant (liquefied petroleum gas) are charged under increased pressure to give a water-based aerosol of each compound.
  • each of the present compounds (1) to (687) is mixed with 0.3 g of d-allethrin, and the mixture is dissolved in 20 ml of acetone.
  • the solution is uniformly mixed with 99.4 g of a carrier for mosquito-coils (prepared by mixing Tabu powder, pyrethrum marc powder and wood flour in the ratio of 4 : 3 : 3) under stirring.
  • the mixture is well kneaded with 120 ml of water, molded, and dried to give a mosquito-coil of each compound.
  • each of the present compounds (1) to (687), 0.3 parts of d-allethrin, and 0.4 g of pipenyl butoxide are dissolved in acetone to have a total volume of 10 ml. Then, 0.5 ml of the solution is uniformly absorbed in a substrate for electric mosquito-mats having a size of 2.5 cm x 1.5 cm and a thickness of 0.3 cm (prepared by forming a fibrillated mixture of cotton linter and pulp into a sheet) to give an electric mosquito-mat of each compound.
  • each of the present compounds (1) to (687) is dissolved in a suitable amount of acetone.
  • the solution is absorbed in a porous ceramic plate having a size of 4.0 cm x 4.0 cm and a thickness of 1.2 cm to give a heating smoke formulation of each compound.
  • a 200-fold water dilution (500 ppm) of a test compound formulation obtained according to Formulation Example 1 or 2 was absorbed at a volume of 2 ml in an artificial diet (Insecta LF available from Nihon Nosan K.K.) having a weight of 13 g, which had been prepared in a polyethylene cup having a diameter of 11 cm.
  • Five fourth-instar larvae of Spodoptera litura were set free in the cup. After 6 days, the survival of the larvae was examined to determine the mortality.

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Claims (28)

  1. Composé oxime de formule (1)
    Figure 06540001
    dans laquelle :
    R1, R2 et R3 sont indépendamment un atome d'halogène, un groupe alkyle en C1 à C3, halogénoalkyle en C1 à C3, alcoxy en C1 à C3, halogénoalcoxy en C1 à C3, nitro ou cyano ;
    R4 est un groupe 3,3-dihalogéno-2-propényle ;
    a est un entier de 0 à 2 ;
    Y est un atome d'oxygène, de soufre de NH ;
    Z est un atome d'oxygène, de soufre ou NR5 dans lequel R5 est un atome d'hydrogène, un groupe acétyle ou alkyle à C1 à C3 ;
    X est X1 ou X2 de formule (2)
    Figure 06540002
    dans laquelle :
    R6 est un atome d'hydrogène, un groupe alkyle en C1 à C8, un halogénoalkyle en C2 à C6, alcényle C3 à C6, halogénoalcényle en C3 à C6, alcényle en C3 à C6, halogénoalcynyle en C3 à C6 ou triphénylméthyle,
       ou cycloalkyle en C3 à C7 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalkylalkyle en C4 à C10 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou cycloalcényle en C5 à C6 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalcénylalkyle en C6 à C8 facultativement substitué par un groupe alkyle à C1 à C4 sur son cycle,
       ou alkyle en C1 à C6 substitué par un groupe cyano, nitro, (alcoxy en C1 à C4)-carbonyle, alkylthio en C1 à C4 ou alcoxy en C1 à C4,
       ou T1-1, T1-2, T1-3, T1-4, T1-5, T1-6 ou T1-7 de formule (3)
    Figure 06550001
    Figure 06550002
    Figure 06550003
    dans laquelle :
    les (R10)b sont zéro à cinq substituants identiques ou différents choisis parmi un atome d'halogène, un groupe alkyle en C1 à C6, halogénoalkyle en C1 à C3, alcényle en C2 à C6, halogénoalcényle en C2 à C6, alcynyle en C2 à C6, halogénoalcynyle en C2 à C6, alcoxy en C1 à C6, halogénoalcoxy en C1 à C3, alcényloxy en C3 à C6, halogénoalcényloxy en C3 à C6, alcynyloxy en C3 à C6, halogénoalcynyloxy en C3 à C6 (alcoxy en C1 à C5)carbonyle, cyano ou nitro ;
    R11, R12, R13 et R14 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
    D est -CH= ;
    J est un atome d'oxygène ou de soufre ;
    b est un entier de 0 à 5 ;
    d est un entier de 1 à 3 ;
    e est un entier de 0 à 3 ;
    f est un entier de 2 à 4 ;
    R15 est un groupe alkyle en C1 à C6, halogénoalkyle en C1 à C3, alcényle en C2 à C6 ou cycloalkyle en C3 à C6, ou un groupe phényle facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C4 ou halogénoalcoxy en C1 à C3 ; et
    R16 et R42 sont indépendamment un groupe alkyle en C1 à C6, halogénoalkyle en C2 à C6, alcényle en C3 à C6, halogénoalcényle en C3 à C6, alcynyle en C3 à C6, halogénoalcynyle en C3 à C6 ou cycloalkyle en C3 à C6,
       ou phényle facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C4 ou halogénoalcoxy en C1 à C3,
       ou benzyle facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C4 ou halogénoalcoxy en C1 à C3 sur son cycle ;
    R7 est un atome d'hydrogène, un groupe alkyle en C1 à C6, halogénoalkyle en C1 à C3, cycloalkyle en C3 à C6, cyano, cyano alkyle en C1 à C3 (alcoxy en C1 à C4)carbonyle ou (alcoxy en C1 à C4)-carbonyle(alkyle en C1 à C3),
       ou phényle facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3,
       ou benzyle facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C4 ou halogénoalcoxy en C1 à C3 sur son cycle ;
    R8 et R9 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C11, halogénoalkyle en C1 à C6, alcényle en C2 à C6, halogénoalcényle en C2 à C6, alcynyle en C2 à C6, halogénoalcynyle en C2 à C6, alcoxyalkyle en C2 à C10, alkylthioalkyle en C2 à C10 ou naphtyle,
       ou cycloalkyle en C3 à C7 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalkylalkyle en C4 à C10 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou cycloalcényle en C5 à C6 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalcénylalkyle en C6 à C8 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
    ou T2-1 ou T2-2 de formule (4)
    Figure 06570001
       dans laquelle :
    les (R17)b sont zéro à cinq substituants identiques ou différents choisis parmi un atome d'halogène, un groupe alkyle en C1 à C6, halogénoalkyle en C1 à C3, alcényle en C2 à C6, halogénoalcényle en C2 à C6, alcynyle en C2 à C6, halogénoalcynyle en C2 à C6, alcoxy en C1 à C6, halogénoalcoxy en C1 à C3, alcényloxy en C3 à C6, halogénoalcényloxy en C3 à C6, alcynyloxy en C3 à C6, halogénoalcynyloxy en C3 à C6, alkylthio en C1 à C3, halogénoalkylthio en C1 à C3, alkylsulfinyle en C1 à C2, alkylsulfonyle en C1 à C2, halogénoalkylsulfinyle en C1 à C2, halogénoalkylsulfonyle en C1 à C2, hydroxyalkyle en C1 à C3, alcoxyalkyle en C2 à C4, alkylthioalkyle en C2 à C4, diméthylamino, acétamido, acétyle, formyle, carboxyle, (alkyl en C1 à C2) aminocarbonyle, [di(alkyl en C1 à C2) amino] carbonyle, (alcoxy en C1 à C6)carbonyle, cycloalkyle en C3 à C6, cycloalcényle en C5 à C6, cycloalkyloxy en C3 à C6, cycloalcényloxy en C5 à C6, pentafluorosulfanyle (F5S), cyano, ou nitro,
       ou phényle facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3,
       ou phénoxy facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3,
       ou benzyle facultativement substitué par un groupe atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3 sur le son cycle,
       ou benzyloxy facultativement substitué par un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3 sur son cycle,
       ou lorsque b vaut 2 à 5, deux R17 adjacents sont combinés ensemble au niveau de leurs extrémités pour former un groupe triméthylène ou tétraméthylène,
       ou lorsque b vaut 2 à 5, deux R17 adjacents sont combinés ensemble au niveau de leurs extrémités pour former un groupe méthylènedioxy facultativement substitué par un atome d'halogène ou un groupe alkyle en C1 à C3,
    ou lorsque b vaut 2 à 5, deux R17 adjacents sont combinés ensemble au niveau de leurs extrémités pour former un groupe éthylènedioxy facultativement substitué par un atome d'halogène ou un groupe alkyle en C1 à C3 ;
    D est -CH=
    R11 et R12 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C8 ou trifluorométhyle ;
    b est un entier de 0 à 5 ; et
    d est un entier de 1 à 3 ;
       ou R8 et R9 sont combinés ensemble au niveau de leurs extrémités pour former un cycle carboné à 5 ou 6 chaínons saturés ou insaturés
    A1 est A1-1, A1-2, A1-3, A1-4, A1-5, A1-6, A1-7, A1-8, A1-9, A1- 10, A1-11 ou A1-12 de formule (5) A1-1 :   -(CR19=CR20)h-(CR21R22)i- A1-2 :   -(CR19=CR20)h-(CR21R22)j-Q1-(CR23R24)k- A1-3 :   -(CR19=CR20)h-(CR21R22)j-Q1
    -(CR23R24)m-CR25=CR26-(CR27R28)n-     A1-4 :   -(CR19=CR20)h-(CR21R22)j-Q1
    - (CR23R24)m-C≡C-(CR25R26)n-     A1-5 :   -(CR19=CR20)h-(CR21R22)j-Q1
    - (CR23R24)p-E-(CR25R26)q-     A1-6 :   -(CR19=CR20)h-(CR21R22)j-Q1
    -(CR23R24)r-Q2-(CR25R26)s-     A1-7 :   -U1-(CR19R20)t-(CR23=CR24)h-(CR25R26)u
    -(CR27=CR28)p-(CR29R30)j-     A1-8 :   -U2-(CR19R20)j-(CR23=CR24)h-(CR25R26)u
    -(CR27=CR28)p-(CR29R30)v     A1-9 :   -U1-(CR19R20)t-(CR23=CR24)h-(CR25R26)j-Q1
    - (CR27R28), -(CR29=CR30)p-(CR31R32)w-     A1-10 :   -U2-(CR19R20)j-(CR23=CR24)h-(CR25R26)v-Q1
    -(CR27R28)w-(CR29=CR30)p-(CR31R32)x-     A1-11 :   -U1-(CR19R20)t-Q1-(CR23R24)h-E-(CR225R26)p- A1-12 :   -U1-(CR19R2O)t-Q1-(CR23R24)j-C≡C-(CR25R26)m-    dans laquelle :
    R19, R20, R21, R23, R24, R25, R26 R27, R28, R29, R30, R31 et R32 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhylène ;
    R22 est un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle,
       ou lorsque h vaut 0 et i vaut 1 dans A1-1, R22 et R7 peuvent être combinés ensemble au niveau de leurs extrémités pour former un groupe triméthylène, tétraméthylène ou pentaméthylène, dont chacun peut être facultativement substitué par un groupe alkyle en C1 à C3,
       ou lorsque h vaut 0 et j vaut 1, dans A1-2, A1-3, A1-4, A1-5 ou A1-6, R22 et R7 peuvent être combinés ensemble au niveau de leurs extrémités pour former un groupe triméthylène, tétraméthylène ou pentaméthylène dans chacun peut être facultativement substitué par un groupe alkyle en C1 à C3 ;
    h est un entier de 0 ou 1 ;
    i est un entier de 1 à 6 ;
    j est un entier de 1 à 3 ;
    k est un entier de 2 à 8 ;
    m est un entier de 1 à 3 ;
    n est un entier de 1 à 3 ;
    p est un entier de 0 ou 1 ;
    q est un entier de 0 ou 1 ;
    r est un entier de 2 à 4 ;
    s est un entier de 2 à 4 ;
    t est un entier de 0 à 3 ;
    u est un entier de 0 à 3 ;
    v est un entier de 1 à 4 ;
    w est un entier de 1 à 4 ;
    x est un entier de 1 à 4 ;
    Q1 est un atome d' oxygène, S(O)y ou NR33 dans lequel R33 est un atome d'hydrogène ou un groupe alkyle en C1 à C3 et y est un entier de 0 à 2 ;
    Q2 un atome d'oxygène, S(O)z ou NR34 dans lequel R34 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et z est un entier de 0 à 2 ;
    E est un groupe cycloalkylène en C5 à C6 ;
    U1 est U1 de formule (6) -G1-W dans laquelle :
    W est un noyau benzène facultativement substitué
    G1 est G1-1 ou G1-2 de formule (7) G1-1 :   -(CR35R36)a1 - G1-2 :   -(CR35R36)b1-Q2- (CR37R38)d1
    dans laquelle : Q2 est un atome d'oxygène, S(O)z ou NR34 dans lequel R34 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et z est un entier de 0 à 2 ; R35, R36, R37 et R38 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
    a1 est un entier de 0 à 4 ;
    b1 est un entier de 1 à 3 ; et
    d1 est un entier de 0 à 2 ;
    U2 est U2 de formule (8) -G1-W-G2-    dans laquelle :
    W est un noyau benzène facultativement substitué
    G1 est G1-1 ou G1-2 de formule (7) G1-1 :   -(CR35R36)a1- G1-2 :   -(CR35R36)b1-Q2-(CR37R38)d1
    dans laquelle : Q2 est un atome d'oxygène, S(O)z ou NR34 dans lequel R34 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et z est un entier de 0 à 2 ;
    R35, R36, R37 et R38 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
    a1 est un entier de 0 à 4 ;
    b1 est un entier de 1 à 3 ; et
    d1 est un entier de 0 à 2 ;
    G2 un atome d'oxygène, S(O)e1 ou NR39 dans lequel R39 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et e1 est un entier de 0 à 2 ;
    A2 est A2-1, A2-2, A2-3, A2-4, A2-5, A2-6, A2-7, A2-8, A2-9 ou A2- 10 de formule (9) A2-1 :   -(CR19R20)j-(CR23=CR24)h-(CR25R26)t
    - (CR27=CR28)p-(CR29R30)m-     A2-2 :   -(CR19R20)j-(CR23=CR24)h-(CR25R26)m-Q1
    -(CR27R28)n-(CR29=CR30)p-(CR31R32)f1-     A2-3 :   -U3-(CR19R20)t-(CR23=CR24)h-(CR25R26)u
    - (CR27=CR28)p-(CR29R30)j-     A2-4 :   -U4-(CR19R20)j-(CR23=CR24)h-(CR25R26)t
    - (CR27=CR28)p-(CR29R30)m-     A2-5 :   -U3-(CR19R20)t-(CR23=CR24)h-(CR25R26)j-Q1
    -(CR27R28)m-(CR29=CR30)p-(CR31R32)n-     A2-6 :   -U4-(CR19R20)j-(CR23=CR24)h-(CR25R26)m-Q1
    - (CR27R28)n-(CR29=CR30)p-(CR31R32)f1-     A2-7 :   -U3-(CR19R20)t-Q1-(CR23R24)h-E-(CRuR26)p- A2-8 :   -U3-(CR19R20)t-Q1-(CR23R24)j-C≡C-(CR25R26)m- A2-9 :   -(CR19R20)h-E-(CR23R24)p- A2-10 :   -(CR19R20)j-C≡C-(CR23R24)m- dans laquelle :
    R19, R20, R23, R24, R25, R26, R27, R28, R29, R30, R31, et R32 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
    h est un entier de 0 ou 1 ;
    j est un entier de 1 à 3 ;
    m est un entier de 1 à 3 ;
    n est un entier de 1 à 3 ;
    p est un entier de 0 ou 1 ;
    t est un entier de 0 à 3 ;
    u est un entier de 0 à 3 ;
    f1 est un entier de 1 à 3 ;
    Q1 est un atome d'oxygène, S(O)y ou NR33 est atome d'hydrogène ou un groupe alkyle en C1 à C3, et y est un entier de 0 à 2 ;
    E est un groupe cycloalkylène en C5 à C6 ;
    U3 est U3-1, U3-2 ou U3-3 de formule (10)
    Figure 06620001
    dans laquelle :
    R35 et R36 sont indépendamment un atome d'hydrogène, un groupe alkyle C1 à C3 ou trifluorométhyle ;
    les (R40)g1 sont zéro à quatre substituants identiques ou différents choisis parmi un atome d'halogène, un groupe alkyle à C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3 ;
    R et V sont -CH=
    g1 est un entier de 0 à 4 ;
    h1 est un entier de 1 à 3 ;
    i1 est un entier de 2 ou 3 ; et
    Q2 est un atome d'oxygène, S(O)z ou NR34 dans lequel R34 est un atome d'hydrogène ou un groupe alkyle en C1 à C3,
    et z est un entier de 0 à 2 ;
    U4 est U4-1, U4-2 ou U4-3 de formule (11)
    Figure 06620002
       dans laquelle :
    R35 et R36 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
    les (R40)g1 sont zéro à quatre substituants identiques ou différents choisis parmi un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3.
    R et V sont =CH=
    g1 est un entier de 0 à 4 ;
    h1 est un entier de 1 à 3 ;
    i1 est un entier de 2 ou 3 ;
    Q2 est un atome d'oxygène, S(O)z ou NR34 dans lequel R34 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et z est un entier de 0 à 2 ; et
    Q3 est un atome d'oxygène, S(O)e1 ou NR39 dans lequel R39 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et e1 est un entier de 0 à 2.
  2. Composé oxime selon la revendication 1, dans lequel X est X1.
  3. Composé oxime selon la revendication 1, dans lequel X est X2.
  4. Composé oxime selon la revendication 2, dans lequel A1 est A1-1, A1-2, A1-3, A1-4, A1-5 ou A1-6.
  5. Composé oxime selon la revendication 2, dans lequel A1-1 et A1-7, A1-8, A1-9, A1-10, A1-11 ou A1-12.
  6. Composé oxime selon la revendication 4, dans lequel Y et Z sont tous deux un atome d'oxygène, a vaut 0 et
       R2 et R3 sont indépendamment un atome d'halogène ou un groupe alkyle en C1 à C3.
  7. Composé oxime selon la revendication 4 ou 6
       dans lequel R6 est un groupe alkyle en C1 à C8, halogénoalkyle C2 à C6, alcényle en C3 à C6, halogénoalcényle en C3 à C6, alcynyle en C3 à C6 ou halogénoalcynyle C3 à C6,
       ou cycloalkyle en C3 à C7 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalkylalkyle en C4 à C10 facultativement substitué par un groupe alkyle en C1 à C6 sur son cycle,
       ou cycloalcényle en C5 à C6 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalcénylalkyle en C6 à C8 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou alkyle en C1 à C6 substitué par un groupe cyano, nitro, (alcoxy en C1 à C4)carbonyle, alkylthio en C1 à C4 ou alcoxy en C1 à C4.
  8. Composé oxime selon la revendication 4 ou 6 dans lequel R6 est un atome d'hydrogène.
  9. Composé oxime selon la revendication 4, 6, 7 ou 8,
    dans lequel R7 est un atome d'hydrogène, un groupe alkyle en C1 à C6, halogénoalkyle en C1 à C3 ou cycloalkyle en C3 à C6.
  10. Composé oxime selon la revendication 4 ou 6,
    dans lequel :
    A1 est A1-2 ;
    k est un entier de 2 à 6 ;
    R6 est un groupe alkyle en C1 à C8, halogénoalkyle en C2 à C6, alcényle en C3 à C6, halogénoalcényle en C3 à C6, alcynyle en C3 à C6 ou halogénoalcynyle en C3 à C6,
       ou cycloalkyle en C3 à C7 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalkylalkyle en C4 à C10 facultativement substitué par un groupe alkyle en C1 à C6 sur son cycle,
       ou cycloalcényle en C5 à C6 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalcénylalkyle en C6 à C8 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
    ou T1-1 ou T1-2 ; et
    R7 est un atome d'hydrogène, un groupe alkyle en C1 à C6,
    ou halogénoalkyle en C1 à C3 ; ou
    dans lequel :
    A1 est A1-1 ou A1-3 ;
    R6 est un groupe alkyle en C1 à C8, halogénoalkyle en C2 à C6, alcényle en C3 à C6, halogénoalcényle en C3 à C6, alcynyle en C3 à C6, ou halogénoalcynyle en C3 à C6, ou cycloalkyle C3-C7 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalkylalkyle en C4 à C10 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou cycloalcényle en C5 à C6 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalcénylalkyle en C6 à C8 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
    ou T1-1 ou T1-2 ; et
    R7 est un atome d'hydrogène, un groupe alkyle en C1 à C6
    ou halogénoalkyle en C1 à C3.
  11. Composé oxime selon la revendication 6,
    dans lequel :
    A1 est A1-1 ;
    R21 et R22 sont tout deux un atome d'hydrogène ;
    h vaut 0 ;
    i est un entier de 3 à 5 ;
    R2 et R3 sont indépendamment un atome de chlore ou un groupe alkyle en C1 à C3 ;
    a vaut 0 ;
    R4 est le 3,3-dichloro-2-propényle ou le 3,3-dibromo-2-propényle ;
    R6 est un groupe alkyle en C1 à C5, halogénoalkyle en C2 à C4, alcényle en C3 à C6 ou halogénoalcényle en C3 à C6 ; et
    R7 est un atome d'hydrogène, un groupe alkyle en C1 à C4 ou trifluorométhyle ; ou
    dans lequel :
    A1 est A1-2 ;
    R21, R22, R23 et R24 sont tous un atome d'hydrogène ;
    h vaut 0 ;
    Q1 est un atome d'oxygène ;
    j vaut 1 ;
    k est un entier de 3 à 6 ;
    R2 et R3 sont indépendamment un atome de chlore ou un groupe alkyle en C1 à C3 ;
    a vaut 0 ;
    R4 est le 3,3-dichloro-2-propényle ou le 3,3-dibromo-2-propényle ;
    R6 est un groupe alkyle en C1 à C5, halogénoalkyle en C2 à C4, alcényle en C3 à C6 ou halogénoalcényle en C3 à C6 ; et
    R7 est un atome d'hydrogène, un groupe alkyle en en C1 à C4 ou trifluorométhyle.
  12. Composé oxime selon la revendication 5, dans lequel Y et Z sont tous deux un atome d'oxygène,
       a vaut 0, et
       R1, R2, et R3 sont indépendamment un atome d'halogène ou un groupe alkyle en C1 à C3.
  13. Composé oxime selon la revendication 5 ou 12,
       dans lequel A1 est A1-7 or A1-8.
  14. Composé oxime selon la revendication 5, 12 ou 13,
    dans lequel R8 est un atome d'hydrogène.
  15. Composé oxime selon la revendication 5, 12 ou 13,
    dans lequel R8 est un groupe alkyle en C1 à C8, halogénoalkyle en C2 à C6, alcényle en C3 à C6 ou halogénoalcényle en C3 à C6.
  16. Composé oxime selon la revendication 5, dans lequel R2 et R3 sont indépendamment un atome d'halogène ou un groupe alkyle en C1 à C3 ;
       R4 est le 3,3-dichloro-2-propényle ;
       a vaut 0 ;
       Y et Z sont tous deux un atome d'oxygène ;
       R6 est groupe alkyle en C1 à C8, halogénoalkyle en C2 à C6, alcényle en C3 à C8 ou halogénoalcényle en C3 à C6.;
       A1 est A1-7 ;
       G1 est G1-1 ;
       a1 vaut 0 ;
       W est le 1,3-phénylène ou le 1,4-phénylène ;
       h et p valent tous deux 0 ; et
       R19, R20, R25, R26, R29, et R30 sont tous un atome d'hydrogène.
  17. Composé oxime selon la revendication 5, dans lequel R2 et R3 sont indépendamment un atome d'halogène ou un groupe alkyle en C1 à C8 ;
       R4 est le 3,3-dichloro-2-propényle ;
       a vaut 0 ;
       Y et Z sont tous deux un atome d'oxygène ;
       R6 est un groupe alkyle en C1 à C8, hàlogénoalkyle en C2 à C6, alcényle en C3 à C6 ou halogénoalcényle en C3 à C6 ;
       A1 est A1-8 ;
       G1 est G1-1 ;
       a1 vaut 0 ;
       G2 est un atome d'oxygène ;
       W est le 1,3-phénylène ou le 1,4-phénylène ;
       h et p valent tous deux 0 ; et
       R19, R20, R25, R26, R29, et R30 sont tous un atome d'hydrogène.
  18. Composé oxime selon la revendication 3, dans lequel R8 et R9 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C11, halogénoalkyle en C1 à C6, alcényle en C2 à C6, halogénoalcényle en C2 à C6, alcynyle en C2 à C6, halogénoalcynyle en C2 à C6, alcoxyalkyle en C2 à C10, alkylthioalkyle en C2 à C10 ou naphtyle,
       ou cycloalkyle en C3 à C7 facultativement substitué par un groupe alkyle en C1 à C4
       ou cycloalkylalkyle en C4 à C10 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou cycloalcényle en C5 à C6 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalcénylalkyle en C6 à C8 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou T2-1 ou T2-2 de formule (4)
    Figure 06670001
       dans laquelle R17, D, R11 R12, b, et d sont tels que définis dans la revendication 1,
       ou R8 et R9 sont combinés ensemble au niveau de leurs extrémités pour former un cycle carboné à 5 ou 6 chaínons saturés ou insaturé.
  19. Composé oxime selon la revendication 3,
    dans lequel Y et Z sont tous deux un atome d'oxygène,
       a vaut 0, et
       R1, R2, et R3 sont indépendamment un atome d'halogène ou un groupe alkyle en C1 à C3.
  20. Composé oxime selon la revendication 3 ou 18, dans lequel A2 est A2-1.
  21. Composé oxime selon la revendication 3, 18 ou 19,
       dans lequel R8 et R9 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C11, halogénoalkyle en C1 à C6, alcényle en C2 à C6, halogénoalcényle en C2 à C6, alcynyle en C2 à C6, halogénoalcynyle en C2 à C6, alcoxyalkyle en C2 à C10 ou alkylthioalkyle en C2 à C10,
       ou cycloalkyle en C3 à C7 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalkylalkyle en C4 à C10 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou cycloalcényle en C5 à C6 facultativement substitué par un groupe alkyle en C1 à C4,
       ou cycloalcénylalkyle en C6 à C8 facultativement substitué par un groupe alkyle en C1 à C4 sur son cycle,
       ou R8 et R9 sont combinés ensemble au niveau de leurs extrémités pour former un cycle carboné à 5 ou 6 chaínons saturés ou insaturés.
  22. Composé selon la revendication 1, qui est la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butanal O-isopropyloxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)peritanal O-isopropyloxime,
       la 6-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)hexanal O-isopropyloxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butanal O-tert-butyloxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentanal O-tert-butyloxime,
       la 6-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)hexanal O-tert-butyloxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butanal O-(2,2,2-trichloroéthyl)-oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentanal O-(2,2,2-trichloroéthyl)-oxime,
       la 6-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)hexanal O-(2,2,2-trichloroéthyl)-oxime
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butanal O-(3,3-dichloro-2-propényle)-oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentanal O-(3,3-dichloro-2-propényle)-oxime,
       la 6-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)hexanal O-(3,3-dichloro-2-propényle)-oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétaldéhyde O-isopropyl-oxime
       la 5- (2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétaldéhyde O-isopropyl-oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétone O-isopropyloxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétone O-isopropyloxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétaldéhyde O-tert-butyl-oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétaldéhyde O-tert-butyl-oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétone 0-tert-butyloxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétone 0-tert-butyloxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétaldéhyde O-(2,2,2-tri-chloroethyl)oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétaldéhyde 0-(2,2,2-tri-chloroethyl)oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétone O-(2,2,2-trichloroethyl)oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétone O-(2 ,2 ,2-trichloro-ethyl)oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétaldéhyde O-(3,3-dichloro-2-propényle)oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétaldéhyde O-(3,3-dichloro-2-propényle)oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétone O-(3,3-dichloro-2-propényle)oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétone O-(3,3-dichloro-2-propényle)oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)méthylbenzaldéhyde O-sec-butyl-oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)méthylbenzaldéhyde O-t-butyloxime
       la 4-(2-(2,6-dichlo-ro-4-(3,3-dichloro-2-propényloxy)phénoxy)éthyl)benzaldéhyde O-sec-butyl-oxime,
       la 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)éthyl)benzaldéhyde O-allyloxime,
       la 4-(2-(2,6-dichlo-ro-4-(3,3-dichloro-2-propényloxy)phénoxy)éthyl)benzaldéhyde O-(3,3-dichloro-2-propényle)oxime,
       la 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyloxy)benzaldéhyde O-n-propyloxime,
       la 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phénoxy)propyloxy)benzaldéhyde O-isopropyloxime,
       la 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phénoxy)propyloxy)benzaldéhyde O-sec-butyloxime,
       la 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phénoxy)propyloxy)benzaldéhyde O-t-butyloxime,
       la 4'-(3-(2,6-dichloro-4-(3,3-diohloro-2-propényloxy)phénoxy)propyloxy)acétophénone O-éthyloxime,
       la 4'-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)propiophénone O-éthyloxime,
       la 4'-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)acétophénone O-éthylcodme,
       la 4'-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)acétophénone O-n-propyloxime,
       la 4-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)benzaldéhyde O-isopropyloxime,
       la 4'-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyloxy)-2,2,2-trifluoro-acétophénoné O-éthyloxime,
       la 4-(trifluorométhyl)benzaldéhyde O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyl)oxime,
       la 4'-(trifluorométhyl)acétophénone O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)pliénoxy)butyl)oxime,
       la triméthylacétaldéhyde O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyl)oxime,
       la 3,3-diméthyl-2-butanone O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyl)-oxime,
       la 3,3-diméthyl-2-butanone O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phénoxy)butyl)oxime,
       la 4-méthyl-2-pentanone O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyl)oxime,
       la 4-méthyl-2-pentanone O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyl)oxime,
       la 3-méthyl-2-butanone O-(5-(2,6-dichloro-4(3,3-dichloro-2-propényloxy)phénoxy)pentyl)-oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butanal oxime, la 5-'(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentanaloxime,
       la 6-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)hexanaloxime,
       la 4-(2,6-dichloro-4(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétaldéhyde oxime,
       la 5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxyacétaldéhyde oxime,
       la 4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxyacétone oxime,
       la 4- (2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)méthylbenzaldéhyde oxime,
       la 4'-((2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)méthyl)acétophénoné oxime,
       la 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)éthyl)benzaldéhyde oxime,
       la 4'-(2-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)éthyl)acétophénone oxime,
       la 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyloxy)benzaldéhyde oxime,
       la 4-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)benzaldéhyde oxime,
       la 4-(5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxy)benzaldéhyde oxime,
       la 4'-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyloxy)acétophénone oxime,
       la 4'-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)acétophénone oxime,
       la 4'-(5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxy)acétophénone oxime,
       la 4'-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyloxy)-2,2,2-trifluoroacétophénone oxime,
       la 4'-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)-2,2,2-trifluoroacétophénone oxime,
       la 4'-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phénoxy)pentyloxy)-2,2,2-trifluoroacétophénone oxime,
       la 4'-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyloxy)gropiophénone oxime,
       la 4'-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)propiophênone oxime,
       la 4'-(5-(2,6-diohloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxy)propiophénone oxime,
       la 4'-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyloxy)benzophénone oxime,
       la 4'-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyloxy)benzophénone oxime,
       ou la 4'-(5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyloxy)benzophénone oxime.
  23. Agent insecticide/acaricide comprenant en tant qu'ingrédient actif un composé oxime selon l'une quelconque des revendications 1 à 21
  24. Procédé pour l'extermination d'insecte, de tiques ou de mites, comprenant l'application aux insectes, tiques ou mites, ou à leurs habitats, d'une quantité efficace d'un composé oxime selon l'une quelconque des revendications 1 à 21.
  25. Composé hydroxylamine de formule (12)
    Figure 06730001
    ou un sel de celui-ci,
    dans lequel :
    R1, R2, et R3 sont indépendamment un atome d'halogène, un groupe alkyle en C1 à C8, halogénoalkyle en C1 à C3, alcoxy en C1 à C3, halogénoalcoxy en C1 à C3, nitro ou cyano ;
    R4 est un groupe 3,3-dihalogéno-2-propényle ;
    a est un entier de 0 à 2 ;
    Y est un atome d'oxygène, de soufre ou NH ;
    Z est un atome d'oxygène, de soufre ou NR5 dans lequel R5 est un atome d'hydrogène, un groupe acétyle ou alkyle en C1 à C3 ;
    A2 est A2-1, A2-2, A2-3, A2-4, A2-5, A2-6, A2-7, A1-8, A2-9, ou A2-10 de formule (9) A2-1 :   -(CR19R20)j-(CR23=CR24)h-(CR25R26)t
    -(CR27=CR28)p-(CR29R30)m-     A2-2 :   -(CR19R2O)j-(CR23=CR24)h-(CR25R26)m-Q1
    -(CR27R28)n-(CR29=CR30)p-(CR31R32)n-     A2-3 :   -U3-(CR19R20)t-(CR23=CR24)h-(CR26R28)u
    - (CR27=CR28)p-(CR29R30)j-     A2-4 :   -U4-(CR19R20)j-(CR23=CR24)h-(CR26R27)t
    (CR27=CR28)p-(CR29R30)m-     A2-5 :   -U3-(CR19R20)t-(CR23=CR24)h-(CR25R26)j-Q1
    -(CR27R28)m-(CR29=CR30)p-(CR31R32)n     -A2-6 :   -U4-(CR19R20)j-(CR23=CR24)h-(CR25R26)m-Q1
    - (CR27R28)n-(CR29=CR30)p-(CR31R32)n-     A2-7 :   -U3-(CR19R20)t-Q1-(CR23R24)h-E-(CR25R26)p- A2-8 :   -U3-(CR19R20)t-Q1-(CR23R24)j-C=C-(CR25R26)m- A2-9 :   -(CR19R20)h-E=(CR23R24)p- A2-10 :   -(CR19R20)j-C≡C-(CR23R24)m- dans lequel :
    R19, R20, R23, R24, R25, R26, R27, R28, R29, R30, R31, et R32 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
    h est un entier de 0 ou 1 ;
    j est un entier de 1 à 3 ;
    m est un entier de 1 à 3 ;
    n est un entier de 1 à 3 ;
    p est un entier de 0 ou 1 ;
    t est un entier de 0 à 3 ;
    u est un entier de 0 à 3 ;
    f1 est un entier de 1 à 3 ;
    Q1 est un atome d'oxygène, S(O)y, ou NR33 dans lequel R33 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et y est un entier de 0 à 2 ;
    E est un groupe cycloalkylène en C5 à C6 ;
    U3 est U3-1, U3-2, ou U3-3 de formule (10)
    Figure 06750001
    dans laquelle :
    R35 et R36 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
       les (R40)g1 sont zéro à quatre substituants identiques ou différents choisis parmi un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3 ;
    R et V sont -CH=
    g1 est un entier de 0 à 4 ;
    h1 est un entier de 1 à 3 ;
    il est un entier de 2 ou 3 ;
    Q2 est un atome d'oxygène, S(O)z, ou NR34 dans lequel R34 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et z est un entier de 0 à 2 ;
    U4 est U4-1, U4-2, ou U4-3 de formule (11)
    Figure 06750002
    dans laquelle :
    R35 et R36 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1 à C3 ou trifluorométhyle ;
       les (R40)g1 sont zéro à quatre substituants identique ou différents choisis parmi un atome d'halogène, un groupe alkyle en C1 à C4, halogénoalkyle en C1 à C3, alcoxy en C1 à C3 ou halogénoalcoxy en C1 à C3 ;
    R et V sont -CH=
    g1 est un entier de 0 à 4 ;
    h1 est un entier de 1 à 3 ;
    i1 est un entier de 2 ou 3 ;
    Q2 est un atome d'oxygène, S(O)z, ou NR34 dans lequel R34 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et z est un entier de 0 à 2 ; et
    Q3 est un atome d'oxygène, S(O)e1, ou NR39 dans lequel R39 est un atome d'hydrogène ou un groupe alkyle en C1 à C3, et e1 est un entier de 0 à 2.
  26. Composé hydroxylamine selon la revendication 25, dans lequel Y et Z sont tous deux un atome d'oxygène ; a vaut 0; et R2 et R3 sont indépendamment un atome d'halogène ou un groupe alkyle en C1 à C3 ; ou un sel de celui-ci.
  27. Composé hydroxylamine selon la revendication 25, dans lequel A2 est A2-1, ou un sel celui-ci.
  28. Composé hydroxylamine selon la revendication 25, qui est le chlorhydrate de O-(3-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)propyl)hydroxylamine,
       le chlorhydrate de O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)butyl)hydroxylamine,
       le chlorhydrate de O-(-5-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)pentyl)hydroxylamine,
       ou le chlorhydrate de O-(6-(2,6-dichloro-4-(3,3-dichloro-2-propényloxy)phénoxy)hexyl)hydroxylamine.
EP98911012A 1997-04-08 1998-03-26 Composes d'oxime, leur utilisation et intermediaires pour leur production Expired - Lifetime EP0975586B1 (fr)

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WO2000041999A1 (fr) * 1999-01-12 2000-07-20 Sumitomo Chemical Company, Limited Derives d'oxime et utilisations associees
JP4045795B2 (ja) * 2001-12-20 2008-02-13 住友化学株式会社 ２，６−ジクロロフェノール化合物の製造法
TW200406370A (en) * 2002-06-28 2004-05-01 Syngenta Participations Ag 4-(3,3-Dihalo-allyloxy)phenoxy alkyl derivatives
TW200406152A (en) * 2002-08-30 2004-05-01 Syngenta Participations Ag 4-(3,3-Dihalo-allyloxy) phenol derivatives having pesticidal properties
AR042344A1 (es) * 2002-12-11 2005-06-15 Syngenta Participations Ag Derivados de 4-(3,3 - dihalo - aliloxi) fenol con propiedades pesticidas
TW200412845A (en) * 2002-12-23 2004-08-01 Syngenta Participations Ag 2,6-dihalo-4-(3,3-dichloro-allyloxy)-benzylalcohole derivatives having insecticidal and acaricidal properties
TW200507752A (en) 2003-06-23 2005-03-01 Syngenta Participations Ag Pesticidally active ketone and oxime derivatives
US6903449B2 (en) * 2003-08-01 2005-06-07 Micron Technology, Inc. Semiconductor component having chip on board leadframe
CN105693523B (zh) * 2016-03-14 2018-11-13 贵州大学 一种含1,1-二氯丙烯的查耳酮类衍生物、其制备方法和用途
DE102016120081A1 (de) * 2016-10-21 2018-04-26 Minimax Gmbh & Co. Kg Verfahren zur Inbetriebnahme und/oder Wartung einer Brandmelder- und/oder Löschsteuerzentrale sowie Vorrichtung dafür

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JPS58150559A (ja) * 1982-03-04 1983-09-07 Sumitomo Chem Co Ltd オキシムエ−テル誘導体、その製造法およびそれを有効成分として含有する殺虫剤
IL75858A (en) * 1984-07-31 1989-02-28 Commw Scient Ind Res Org Substituted benzyl ethers of oximes,their production and their use as arthropodicides
US4647698A (en) * 1984-09-13 1987-03-03 Sandoz Ltd. Novel compositions
JPS62252756A (ja) 1986-04-25 1987-11-04 Nippon Soda Co Ltd オキシムエ−テル誘導体とその製造方法及び殺虫剤
DE4213149A1 (de) * 1992-04-22 1993-10-28 Hoechst Ag Akarizide, insektizide und nematizide substituierte (Hetero)-Aryl-Alkyl-ketonoxim-O-ether, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel
JP3834838B2 (ja) * 1994-08-04 2006-10-18 住友化学株式会社 ジハロプロペン化合物、それを有効成分とする殺虫、殺ダニ剤およびその製造中間体
DE69505490T2 (de) * 1994-08-04 1999-06-24 Sumitomo Chemical Co., Ltd., Osaka Dihalopropenverbindungen, sie enthaltende insektizide/akarizide mittel, und zwischenprodukte
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TW530041B (en) 2003-05-01
AU6517998A (en) 1998-10-30
US6437184B1 (en) 2002-08-20
DE69827939D1 (de) 2005-01-05
EG22402A (en) 2003-01-29
WO1998045254A3 (fr) 1999-08-26
US20020019569A1 (en) 2002-02-14
TW200300408A (en) 2003-06-01
WO1998045254A2 (fr) 1998-10-15
EP0975586A2 (fr) 2000-02-02
US6448444B2 (en) 2002-09-10

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